New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities

Abstract

A new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisoxazoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparum ( P . f .) (FcB1), and for antimicrobial activity against representative bacterial and fungal strains, as well as for cytotoxicity on MCF7 human breast cancer cells. Given the log P calc and selectivity index values (cytotoxicity/antiplasmodial activity ratio), the benzo[ c ]isoxazol-3-ylmethylene-phenyl-amine ( 11 ) (imino-benzisoxazole) was identified as the best hit against P . f . (FcB1), and the benzo[ c ]isoxazol-3-yl-phenyl-methanone ( 3 ) (3-acyl-2,1-benzisoxazole) against P . f . and the Geotrichum candidum fungal strain.